After releasing two albums near the end of the boy band fad of the late 1990s and early 2000s, the group disbanded in 2003. They began to reform in 2013 as a quartet after Ashley Parker Angel turned down the offer.

O-Town was assembled for the first season of the ABC reality television series Making the Band. Originally Ikaika Kahoano was one of the five members selected but he and his family decided he should go to med school instead causing him to back out, making way for Dan Miller who was selected by the four remaining members. The ratings of Making the Band were strong enough to warrant a second (and eventually third) season. These subsequent seasons depicted their development as a pop group, following their tours and performances etc. Such events included the development of their second album, O2, their transition to a new record label (J Records), and an ongoing struggle to "prove themselves" as legitimate artists. The third season of Making the Band was broadcast on MTV, instead of the original network, ABC.

After season one, Clive Davis of J Records signed O-Town to his new label. Davis believed in the marketability of the group, and scheduled O-Town to be the label's debut act. Their first release, the eponymousO-Town, boosted by the publicity of the weekly television series, sold more than one million copies. Their first single, "Liquid Dreams", was the first single to reach number 1 on the Billboard singles sales chart without making the Airplay chart. The single managed to peak at number 10 on the Billboard Hot 100 chart.

However, their novelty as television personalities soon wore off, and O-Town would enjoy only temporary success. Jacob Underwood even commented, on a Making the Band recap of seasons one and two, that after "Liquid Dreams", they alone had to prove themselves to the public that they weren't a "flash-in-the-pan" success. In the late spring of 2001, O-Town released "All or Nothing" (July 21, 2001), and the song became their biggest hit of their career as a group. "All or Nothing" reached #3 on the Billboard Hot 100 and the song was nominated for numerous awards, including "Song of the Year" during the 2001 Radio Music Awards. The success of "All or Nothing" granted them the ability to air another season of Making the Band. Near the end of the third season, O-town fans and television viewers watched as they tried to take their careers to the next level by writing their own music, earn the respect of their industry peers, and market themselves beyond being labeled as a "boy band". They never found the market acceptance they sought.

Their second album, O2, originally scheduled for the summer of 2002 (and planned debut single "I Showed Her" a few weeks before release), was delayed numerous times, and as time between their last U.S. single, the moderately successful "We Fit Together", and the anticipation of "O2", without any new singles to get radio airplay and no new episodes of Making the Band, the popularity of O-Town began to wane.

O-Town had burst onto the scene when boy bands and other types of bubblegum pop were beginning to decline and lose their influence. Sales of O-Town's second album, O2, were below expectations. Their debut single for O2, "These are the Days" eventually broke into the Billboard Top 40 at 40, and critics, such as those from Billboard.com, praised their second single, "I Showed Her" for being a well-developed song. Despite this moderate success, "O2" was nowhere near the commercial success of their first album, O-Town, and the band went on tour in the summer of 2003 to promote the album. J Records dropped the band from the label in November 2003.

Though fans tried to organize campaigns to get O-Town signed to a new label,[citation needed] their efforts met with little success. The group disbanded in late 2003, and O-Town sent a personal e-mail to all their fans, via the now defunct Inside O-town.com, thanking them for the great memories and experience they had shared together. In the e-mail, O-Town themselves stated that they had disbanded due to the changing climate of the music industry, along with certain financial problems, hinting that Lou Pearlman and his company, Trans Continental Records, may have been involved with these issues. At that point, Pearlman had already experienced many legal challenges by previous acts managed by his company, Trans Continental, including highly successful acts such as the Backstreet Boys, 'N Sync, and Aaron Carter.

The members of O-Town moved on to solo careers. The most successful member of the group has been Ashley Parker, who was signed to Universal's Blackground Records, and also given his own reality show on MTV, There and Back. Released in 2006, Ashley's solo debut album was heavily promoted, but did not achieve solid sales numbers. In January 2007, he began playing the role of Link Larkin in the Broadway production of Hairspray. Ex-bandmate, Trevor Penick, now professionally known as "Tre Scott", was signed to Mach 1 Music, and worked with established industry producer Eddie Galan. The other band members retained a fanbase and had success in their own right, as evidenced by their Myspace profiles. Erik stayed in the music business and went on to collaborate and co-write songs for other artists. Jacob Underwood went on to start his own country band "Jacobs Loc".

Back in January 2011, rumors were swirling that a reunion was in the works for the band. TMZ reported that Erik, Trevor, Dan & Jacob have returned to the studio to record the follow-up to O2, however, it was confirmed that Ashley Parker Angel declined the offer from the guys. He told TMZ in a following article his explanation. "O-Town was one of the greatest chapters of my life, so when the idea of a reunion was brought to me, of course I was intrigued. However I have made the decision not to be a part of an O-Town reunion. It was a difficult decision, but ultimately necessary to move on with the next chapter of my career." [1] He has, however, given the guys his blessing for them to reunite without him. When interviewed about his rejection, Erik said that the guys eventually come to terms with it, but admitted "I would just think he would want to come on board and be a part of it ... but he doesn't and that's cool." [2]

The remaining guys continued to pursue the reunion over the next few years, keeping details very private.

In October 1, 2013, O-Town launched both Twitter and Facebook official pages which was confirmed by Erik, Trevor, Dan & Jacob to be the place for news on the group going forward. It is rumoured the boys are working with record producer Mark Suhonen based out if San Diego and have signed a new record deal and will be releasing an album in 2014. On March 24, 2014, O-Town launched OTownOfficial.com with a countdown clock. When the countdown ended on March 31, it was officially confirmed that they would be going out on their first tour in over a decade during the summer, followed by an album.

On May 28, 2014, O-Town released a preview of the single "Skydive" on SoundCloud. The single is from their third studio album Lines & Circles. The album was released on August 24, 2014.[3]

Nearly three years after O-Town ceased to exist, the Japanese group w-inds covered O-Town's "All or Nothing", calling it "Kaze Uta" (or "Wind Song"). "Kaze Uta" was released on May 25, 2006 on w-inds' single for the song "Trial". While the melody was retained, the lyrics were completely reworked by Takamitsu Shimazaki, and are predominantly in Japanese with a less repetitive chorus. In 2006, Irish boyband Westlife also covered "All or Nothing" on their eighth studio album The Love Album. The American punk band Fake ID also covered it in an upbeat, pop-punk fashion for the compilation album Punk Goes Pop.